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The case the revenue function made when it bought the last decade of tools was that visibility would produce alignment. It has not.

You have more visibility than you have ever had. More dashboards. More integrations. More attribution. More forecasting. More intelligence layered on top of the CRM. The room has more data than ever and is no closer to a decision.

You bought what the category promised. You did not buy what your leadership team needed. The gap between the two is where most of your operating margin pressure is hiding right now.

The Case That Did Not Hold

The pitch was simple. If sales, marketing, and finance could see the same numbers, in the same dashboards, in real time, they would reach the same conclusions. Visibility would close the alignment gap. The tools would do the work the system underneath them was not doing.

The pitch assumed accountability would come out of the data. It did not. Accountability is not a property of the data. It is a property of the system the data sits inside. And the system did not change when the tools were bought.

You are now ten years into this. The platforms are in place. The dashboards are loading. The data is current. The leadership team is still spending the first thirty minutes of every operating review figuring out what the data means.

The case quietly stopped working. The spend continued.

Why Dashboards Become Forums

A dashboard is supposed to be an instrument. You look at the reading and you make the decision. The dashboard does not make the decision. The system around the dashboard does.

When the system around the dashboard is not designed to produce a decision, the dashboard becomes something else. It becomes a forum. A place where functional leaders gather, each with a slightly different read of the same data, each defending the read that protects their function’s number. The dashboard is no longer an instrument. It is the conference table the conversation is happening on.

You have spent the last decade buying dashboards. You are now in this position. The data is good. The integrations work. The numbers are accurate. The conversation is still a negotiation.

There is a specific moment where this becomes visible. The Monday pipeline review opens. Six dashboards are on the screen. The CFO sees one story in the data. The VP of Sales sees another. The VP of Marketing sees a third. Each is reading the same numbers. Each is reaching a different conclusion. The meeting ends with three follow-ups and no decision.

That is not a data problem. It is the predictable output of buying instruments while the system around them was never deliberately designed.

The Accountability Layer That Was Never Built

The reason visibility did not produce alignment is that the BI category and the revenue intelligence category were never selling alignment. They were selling visibility. Alignment is a different thing.

Alignment needs things the dashboards cannot supply. Shared definitions of what the data means before the meeting starts, not invented during it. Clear ownership of what decisions the data should produce. A structured cadence where the operating model brings shared decisions into the meeting and the dashboards confirm them.

None of those are things the platform can deliver. They are things the system around the platform is supposed to deliver. And the system has to be deliberately designed to produce them. It does not happen by buying more capability.

This is the layer that was never built. The spend went into visibility because visibility was buyable. The accountability layer was harder to buy because it was not a product. It was a design choice. And the design choice was deferred quarter after quarter while the dashboard spend grew.

The spend is significant by now. The design choice has not been made. You are sitting on the result.

The Takeaway

Visibility was supposed to produce alignment. It produced a longer conversation.

The platforms did what they were sold to do. The leadership team is doing what it has always done. The gap between what the platforms produce and what the leadership team needs is where the operating model was supposed to live, and where it is currently missing.

This is the question worth asking in your next pipeline review. How many of the dashboards on the screen produced a decision, and how many produced a follow-up?

The honest answer is the diagnosis.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,
Jeff
RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together.

Ask a revenue leader why an underperforming function has not closed the gap and you will hear the response…

More coaching. More enablement. More performance management. More training. Sometimes more hiring.

The response is responsive, measurable, and reportable. The response feels like leadership.

It is also how design problems become permanent.

The Institutional Reflex

The reflex toward people-layer investment is not irrational. It works at the surface level.

A new enablement program produces visible engagement. A new coaching contract produces measurable participation. A new performance management process produces clear documentation. Each investment generates outputs that satisfy the executive review cycle.

What none of them produce is a change in the underlying conditions that made the investment necessary.

What makes the reflex so durable is that it is highly defensible. A VP of Sales asked why the gap persists can point to:

• Enablement spend

• Manager hiring

• Performance management investment

• External coaching contracts

The CFO sees the spend. The CEO sees the leadership effort. The diagnosis stays at the people layer because that is where the response sits.

Why the Reflex Persists

There are structural reasons the response is so durable.

People-layer investment can be deployed quickly. A new enablement program launches in a quarter. A coaching contract starts within a month.

Design-layer change cannot. Redesigning incentive structures or accountability infrastructure takes years of leadership alignment and political capital.

The leadership team confronting an underperforming function has two options on different timelines. Invest in the people layer now, or begin design-layer work that may not produce visible results until next year.

People-layer investment also fits the existing review cadence. The monthly operating review is already running. Adding a coaching program or performance management process gives the next review something concrete to discuss.

Design-layer change does not fit cleanly into a monthly operating review. It requires its own governance and its own success metrics.

There is a third reason the reflex is durable, and it is rarely named. Design-layer change requires the leadership team to acknowledge that prior design decisions, often their own, produced the current problem.

People-layer investment does not require that acknowledgment.

How the Reflex Compounds

Each round of people-layer investment adds capability infrastructure that becomes load-bearing on the original design failure.

The pattern shows up consistently:

• Enablement teams that started as small support functions become full departments with budget, headcount, and quarterly objectives

• Performance management programs instituted to address one gap calcify into HR-owned processes that resist modification

• External coaching contracts that were one-time engagements become recurring line items

• Training curricula built to address specific capability gaps grow into multi-week onboarding programs that take longer to complete each year

None of this is wrong on its own. Each investment was rational at the time it was made.

The compounding consequence is that the people-layer infrastructure becomes its own constituency. By the time leadership recognizes that the design layer is the actual problem, the people-layer investment has acquired its own defenders, its own budget cycles, and its own organizational gravity.

The architectural change that should have happened in year one now has to navigate the people-layer infrastructure that accumulated in years two through five.

This is how stable misalignment becomes durable misalignment.

What the Reflex Conceals

The financial visibility problem surprises leadership teams when it surfaces.

People-layer investment is highly visible in the financials. Enablement budgets, training spend, manager headcount, coaching contracts all appear as legible line items. The CFO can track them quarter over quarter.

The design failure underneath is invisible. There is no line item for:

• A handoff that was never designed

• An incentive structure that produces parallel work

• A goal architecture that segments ownership

• A measurement system that rewards function over outcome

The cost of these design failures is real and large. It does not appear anywhere on a standard operating review.

What appears instead is the cost of the compensation. The enablement budget growing in line with revenue. The performance management investment scaling with headcount. The coaching contracts renewing year over year.

Each line item is defensible. Together they constitute a hidden subsidy from the people layer to the design layer that leadership has not made structural.

The Takeaway

The reflex toward people-layer investment looks like leadership because it is responsive, measurable, and reportable. It is also how design problems become permanent.

The work is not to stop investing in the people layer. Coaching, enablement, performance management, and hiring are necessary.

The work is to recognize when the investment is doing structural repair work that the design layer should be doing on its own.

The line items in your operating budget that have grown most consistently over the last three years are saying something about your design. Fast-growing people-layer spend tends to map to the deepest unaddressed design failures.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff.

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together.

Shared goals are a design output, not a leadership decision.

Many revenue organizations treat shared goals as a leadership move. The CEO names a number. The functional leaders commit to it together. The deck reflects collective ownership. The goal is shared because leadership said so.

It is not. A goal is shared when the operating model makes it structurally inevitable that no function can deliver its own number while the joint outcome misses. Anything less is a target with social agreement on top.

The difference between these two states is invisible until pressure hits. Then it is the only thing in the room.

The System Underneath the Slide

When a revenue leadership team commits to a shared goal, three design questions determine whether the commitment is structural or social:

• Are the inputs to the goal owned jointly, or sequentially handed off?

• Do the constraints connect across functions, or run independently?

• Do the consequences of a joint miss travel back to the functions that produced it, or diffuse upward to the CEO?

Inputs. Marketing produces leads, sales converts them, customer success retains them. When those inputs are owned in sequence, with each function handing off to the next, the goal is parallel work with a shared label. Sales can hit its number. Marketing can hit its number. Customer success can hit its number. The joint outcome is whatever the sequence happens to produce.

Constraints. When marketing’s MQL target is independent of the conversion rate sales experiences, the constraint that should link the two functions is missing from the system. The failure cuts both ways. Marketing can over-produce volume that sales cannot work. Sales can set qualification criteria without marketing’s input, producing demand expectations marketing cannot generate at scale. In either direction, two functions can hit their numbers while the system underperforms.

Consequences. When marketing gets reviewed for MQL target and sales gets reviewed for quota, the consequence of the joint miss has no owner. It diffuses across the leadership team and is absorbed by the CEO at the next monthly operating review.

These three questions determine the actual system. The deck reflects what leadership wanted. The system reflects what the company actually built.

Three Decisions Underneath

The system is rarely designed deliberately. Three decisions produce it, none of them framed as design choices at the time:

• The functional KPI structure set in annual planning

• The review cadence that puts joint synthesis in the CEO’s head, not in the operating model

• The compensation structure that pays against functional outcomes, not joint ones

KPIs. Many revenue organizations set KPIs by function during annual planning. Marketing gets MQL targets, pipeline contribution, brand metrics. Sales gets quota, pipeline coverage, win rate. Customer success gets retention, expansion, NPS. Each KPI is owned by the function it measures. The system between them goes unmeasured. The decision to structure KPIs by function, made every year in planning, is the decision that produces shared goals without shared accountability.

Cadence. Functions review their own results in their own meetings. The shared review happens at the monthly operating review, where each function presents their numbers and the leadership team synthesizes across them. The synthesis is the moment where joint accountability could live. In many companies, it happens after the presentations, in the CEO’s head, and gets converted into the next set of priorities. The joint accountability work is real but invisible. The system has no name for it.

Compensation. Functional leaders are compensated against functional outcomes. Bonuses, equity refreshes, and promotions track functional performance. The joint outcome the slide claims everyone is responsible for is owned by no one when the compensation conversation happens. The compensation structure tells functional leaders, with money, what they are actually accountable for. The deck tells them what to say in the meeting.

These three decisions, made independently and rarely connected, produce shared goals in name only. None is wrong on its own. Together, they design parallel work with a shared label.

Why This Persists

The deeper question is why this system persists when the consequences are well understood. The answer is that the system is harder to change than the symptoms.

Functional KPIs are how leadership teams manage performance at scale. The review cadence is built around the operating rhythm of the business. The compensation structure is anchored in market norms and retention dynamics. Each is load-bearing. Changing any one of them creates risk in dimensions the leadership team is currently managing successfully.

So the symptoms get treated instead. A new dashboard that visualizes the joint outcome. A cross-functional steering committee. A go-to-market alignment workshop. Each is a process intervention on top of an unchanged system. Each typically runs through marketing’s discretionary budget, which means the function most often blamed for misalignment also funds the treatment of its symptoms. The shared goal continues to underperform. The leadership team continues to invest in synthesis work the system should be doing.

The result is a stable disequilibrium. The system produces predictable misalignment. The symptoms produce predictable management responses. Both are functioning exactly as designed.

The Takeaway

Shared goals are not a leadership posture. They are an output of three design choices: how inputs are owned, how constraints connect, and how consequences travel.

When all three are structural, the shared goal becomes inevitable. When any one is left to social agreement, the goal becomes a target with leadership commitment on top.

The work is not to commit to shared goals more sincerely. The work is to examine the system that produces them. Which of the three is structural in your organization? Which is social? And what would it take to move one from one column to the other?

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together.

Every quarter, sustaining your revenue results requires a little more effort than the quarter before. Planning meetings run longer than they did a year ago. Forecast reviews start with reconciliation instead of decisions. Handoffs between sales and marketing require more follow-up than anyone remembers needing before. The best operators on both sides of the revenue table spend increasing portions of their week compensating for gaps that have never been formally addressed.

The results still come in. That is what makes this condition easy to miss. The organization is not failing. It is absorbing a compounding structural cost that most leadership teams have never examined, because performance has given them permission to defer the examination. That condition has a name: misalignment debt.

What Misalignment Debt Actually Looks Like

The debt accrues silently because the organization continues to perform. Performance becomes the reason nobody examines what that performance is costing.

It shows up in specific, recognizable patterns:

• A VP of Sales spends hours every month coaching reps through handoff confusion that would not exist if ownership between functions were clearly defined

• A VP of Marketing builds enablement programs and pipeline development initiatives that sales never engages with, then spends hours defending the value of work the system was never designed to connect to revenue

• Forecast reviews begin with fifteen minutes of reconciliation about whose numbers are right before any decision about what to do next can begin

• Opportunities enter the pipeline with momentum and then slow once they cross from marketing to sales, not because the leads were wrong but because the system that receives them was not designed to continue what marketing started

None of this appears on a P&L. All of it consumes the most constrained resource in the business: leadership time and attention.

The debt removes capacity not in large, visible increments but in thirty-minute blocks scattered across every week. Each one reasonable. Each one absorbed. Each one recurring. Every hour a revenue leader spends compensating for a design gap is an hour unavailable for growth decisions, strategic clarity, or the work that only they can do.

Why the Debt Stays Hidden

Misalignment debt persists because acceptable performance gives leadership permission to defer. Deals close. Revenue comes in. The business grows. The trajectory beneath those results tells a different story.

Sales cycles stretch without a clear explanation. The organization absorbs the delay as a market condition or a buyer behavior shift rather than recognizing it as a design condition inside their own system. Leaders spend time diagnosing external causes for a problem that lives inside the operating model.

As the debt accumulates, forecast reliability quietly degrades. Forecast accuracy depends on consistent definitions, clean stage criteria, and shared agreement on what constitutes a qualified opportunity. When those standards differ across functions, the forecast reflects a negotiated consensus rather than an operating reality. Leadership makes decisions based on numbers that required reconciliation to produce, which means the confidence behind those decisions is lower than it appears.

The response to declining confidence is predictable: more oversight, more checkpoints, more executive involvement in deals that should move without intervention. The system becomes dependent on a smaller number of experienced operators who know how to read past the data and make judgment calls the formal process cannot support.

When one of those operators leaves, the organization discovers within a quarter what the system was actually designed to produce without their compensation.

The Debt Does Not Reset When Leadership Changes

This connects to something the mid-market organizations I watch closely tend to underestimate. When a VP of Sales or VP of Marketing transitions out and a new leader arrives, the debt does not reset. It transfers intact.

The new leader encounters friction that should have clean answers, asks questions the organization has been deferring, and begins the same diagnostic work their predecessor started. If the organization misdiagnoses the friction as a fit problem or a talent gap, it replaces the leader and the cycle begins again.

The debt does not accumulate because people failed. It accumulates because the system was built through addition, not architecture. New processes layered on old assumptions. New tools connected to legacy definitions. New leaders inheriting operating models they did not design and cannot fully see.

The system outlasts the leader. The debt outlasts the transition.

The Bottom Line

The organizations that break this cycle share one characteristic. They stop treating the symptoms of misalignment debt as individual problems to manage and start treating the system that produces them as a design problem to solve. They do not add more coordination, more meetings, or more reporting. They examine the operating model that makes those interventions necessary in the first place.

That examination is not a quick fix. It is not a reorganization. It is a deliberate redesign of how revenue work runs across the organization, starting with the foundational conditions that determine whether alignment holds under pressure or collapses the moment leadership attention moves elsewhere.

The debt is structural. It is compounding. And it is already being paid inside your organization, distributed across leadership calendars, embedded in deal timelines, and hidden inside forecasts that look defensible but cost more to produce every quarter.

The only decision is whether to keep servicing it or redesign the system that produces it.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together

The revenue organization is hitting its number. Pipeline is moving. Deals are closing. The forecast comes in close enough that leadership does not ask too many questions. If you looked only at the results, you would call it a healthy system.

Look closer and the picture changes. A small number of people inside that organization have learned how to make the system produce those results. They know which handoffs to watch because those handoffs break without supervision. They know whose forecast numbers to question because the CRM data is inconsistent and they have learned where the gaps live. They know when to escalate and when to absorb because the formal process does not account for the judgment calls that actually move deals forward.

The organization performs because they perform. That is not organizational strength. It is organizational fragility wearing the face of competence.

When Effort Becomes the Operating System

When a revenue system depends on certain individuals to function normally, the system was not designed to produce its current results. It was designed to require those individuals to produce them on its behalf. That distinction changes what leadership should be solving for.

Most organizations read strong individual performance as a talent story. They reward the operator. They build retention plans around them. They structure teams to keep them in place. None of that is wrong. But none of it addresses the underlying condition either.

The underlying condition is effort substitution. The system has gaps the design never closed, and specific people learned to fill those gaps through judgment, relationships, institutional memory, and sheer repetition. Over time, their compensation becomes load-bearing. The organization does not just benefit from their effort. It depends on it to function at the level leadership expects.

This is not a sales-side problem or a marketing-side problem. It is a system-level condition that shows up differently in each function. On the sales side, it looks like a senior AE who informally runs forecast reconciliation because the CRM cannot be trusted. On the marketing side, it looks like a demand gen leader who translates campaign data into language sales will act on because the reporting infrastructure was never designed to do it. Both are compensating for gaps the design left open. Both are load-bearing.

This dependency accumulates quietly. It does not show up in a dashboard. It does not appear in a quarterly review. It compounds in the background as the organization grows: each new rep requires more onboarding oversight from the same operators, each new market layer requires more cross-functional coordination the design was never built to handle, each new product creates more handoff ambiguity that gets resolved by the same people who resolved it last time.

The results continue. The effort required to produce them increases. And because the results continue, leadership has no structural reason to question the design. The system appears to be working. The people inside it know better.

What a Departure Reveals

The clearest test for effort substitution is not an audit. It is a departure.

When the person who was informally holding part of the revenue system together leaves, the organization discovers within one to two quarters what the design was actually capable of producing on its own. The forecast softens. Handoffs that used to be seamless start requiring escalation. Deals that moved through the pipeline without friction begin stalling at stages no one previously monitored.

The institutional knowledge that person carried disappears with them: which relationships to protect, which data to question, when to intervene and when to let a process run. Leadership responds the way most organizations do. The backfill search focuses on replicating capabilities. The assumption is that the role needs a stronger hire.

That assumption is worth questioning. The departed person did not produce those results because the system supported them. They produced those results because they learned to compensate for where the system could not. The role was never designed to deliver what they delivered. It was designed to require someone like them to deliver it.

The Compounding Cost Most Leaders Never See

The performance dip after a key departure is the first-order cost. It is real but recoverable. The second-order cost is harder to see: more management layers, more oversight cadences, more reporting checkpoints added to stabilize what one person used to hold together informally. The system gets heavier. The overhead increases. The effort required to produce the same result compounds further.

The third-order cost is the one that rarely gets named. The organization loses the capacity to see the design problem clearly because the layers of compensation have become the design. What started as individual workarounds became team norms. What started as team norms became operational assumptions. What started as assumptions became invisible infrastructure that no one remembers choosing and no one knows how to change.

In the mid-market organizations where this pattern is the most acute, the compounding is accelerated by scale. A 200-person company growing at 15 to 20 percent annually is adding coordination complexity faster than it is adding capacity. If the system was not designed to absorb that complexity, the load falls on the operators who already know how to compensate. They absorb more. They adapt. They hold. Until they cannot. Or until they leave. Or until the organization tries to scale past what effort substitution can carry and discovers the ceiling the design was always going to produce.

The Question Worth Sitting With

Your revenue system is probably working. The question is what in that system is currently working because of who is doing it rather than how it was designed.

If the answer involves specific names, specific relationships, or specific people whose departure would expose gaps the organization has never formally addressed, the system is not producing those results. Those people are. And the longer the organization treats that as a talent story instead of a design condition, the higher the cost of eventually redesigning around it becomes.

The goal of deliberate system design is not to replace exceptional people. It is to stop requiring them to compensate for what the design cannot produce. That shift does not diminish their contribution. It protects it by building a system worthy of the people operating inside it.

If this landed close to home, I would like to hear which part. Hit reply.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week, Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together

Most revenue leaders have run at least one alignment initiative that produced real results. Pipeline reviews got cleaner. Handoff friction that had been slowing deals decreased. Sales and marketing were communicating better than they had in years. For a quarter or two, the organization operated with a shared sense of direction that had been missing.

Then the quarter got busy. A major deal demanded leadership attention. A product launch accelerated the marketing calendar. The end of period push consumed the sales team. Nobody decided to stop working on alignment. It just quietly moved down the priority list.

Within two quarters, the same friction was back.

When that happens, leadership makes a familiar diagnosis: the team lost focus, the initiative lost sponsorship, the follow-through was not strong enough. That diagnosis leads directly to a decision — launch a new initiative, with tighter accountability and stronger executive commitment this time.

The diagnosis is wrong. And the cost of staying inside it compounds with every cycle.

What the Initiative Was Actually Doing

An alignment initiative does not change how a revenue organization is designed to operate. It adds a layer of coordinated effort on top of the existing design.

That layer is real and the results it produces are genuine. When someone is actively holding the coordination together, behavior changes. Meetings become more productive. Handoffs improve. Definitions get clarified in the room even if they are not formally documented. The initiative produces results because capable people are making it produce them.

The problem surfaces the moment that effort is withdrawn.

Remove the initiative and you reveal the design underneath. The incentive structures that reward different outcomes across functions are still in place. The handoff rules that create ambiguity at the same points every quarter are still operating. The definitions that shift depending on who is in the room are still ungoverned. The initiative covered those conditions temporarily. It never changed them.

This is the structural reality most organizations have not named. The initiative was compensating for a design gap. When the initiative ends, the gap remains. The friction it was covering returns because it was never resolved. It was managed.

The Cost That Compounds Across Cycles

The individual cost of a single faded initiative is manageable. A quarter or two of improved behavior followed by a return to baseline is disappointing but not catastrophic.

The compounding cost across multiple cycles is a different problem entirely.

Each initiative cycle consumes something the organization does not fully account for. Leadership credibility is spent each time an initiative is launched with genuine commitment and then fades. Team trust erodes each time the same problems return after a concerted effort to fix them. Organizational energy is drawn down each time capable people invest in an effort that does not hold. Over three or four cycles, the organization becomes quietly skeptical of alignment efforts, not because the people are cynical, but because the pattern has taught them that alignment is temporary by nature.

It is not temporary by nature. It is temporary by design. Specifically, by the absence of a design that makes it durable.

What a System Produces That an Initiative Cannot

The distinction between an initiative and a system is not about scale or complexity. It is about what each one is structurally capable of producing.

An initiative changes behavior through sustained human effort. A system changes behavior through design. The incentives, the definitions, the handoff rules, the decision rights: when those are set deliberately and governed consistently, they produce their outputs regardless of whether anyone is paying attention that week. Aligned behavior becomes what the organization defaults to, not what it achieves through sustained effort.

The observable difference inside organizations that have made this shift is specific. Leadership time is not consumed by resolving the same definition debates and ownership questions each quarter, because those were settled at the design level rather than managed through repeated conversation. New leaders who join the organization can operate within a clear system rather than spending their first two quarters learning the informal workarounds. Pressure does not erode alignment because the design was built to hold under pressure, not just under ideal conditions.

Most organizations have never built that. Not because they did not want to. Because they kept reaching for the initiative when the design was what needed to change. The initiative felt faster, it produced visible results sooner, and it did not require the harder leadership conversation about what the organization was actually designed to produce.

The Question Worth Sitting With

The organizations that no longer need alignment initiatives are not the ones with the best people or the strongest relationships. They are the ones that stopped treating alignment as something to manage and started treating it as something to design.

That shift starts with a question most leadership teams have never formally asked: what would have to be true about the design of our revenue system for an alignment initiative to no longer be necessary?

If the answer is unclear, the next initiative will produce the same result as the last one. Not because of the people involved. Because the design underneath it has not changed.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week, Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together

Ask a revenue leader to describe their culture and you will hear something about values. Collaboration. Accountability. Customer focus. The right words.

Ask them what their culture actually produces at the moments that matter most — the handoff that stalls, the forecast conversation that stays positive when it should not, the definition debate that gets avoided again — and the answer is usually less clear.

That gap is the problem. Not the values themselves, but the distance between what leaders say the culture is and what it actually does when work gets hard.

Culture Is Not What You Post on the Wall

Culture inside a revenue organization is not a values statement. It is the set of unwritten decision rules that govern what people actually do at the moments where the formal system cannot give them a clear answer.

When a lead reaches the handoff point and nobody owns the next step, something decides whether someone acts or waits. When a forecast number feels wrong but surfacing it means a difficult conversation, something decides whether it gets named or carried quietly. When a definition debate resurfaces for the third time, something decides whether anyone pushes for resolution or avoids it again.

That something is culture. Not the values on the wall. The rules in the room.

Those rules are operating right now in your revenue organization. The question is whether anyone chose them.

How the Rules Get Set Without Anyone Deciding

In most revenue organizations, the decision rules governing these moments were never formally set. They formed over time. From what got rewarded during a difficult quarter. From what went unaddressed when it should not have. From the habits and instincts of whoever had the most influence when the patterns took hold.

This is where the leader dependency problem shows up. When culture forms around a specific leader’s personality and preferences rather than a deliberate design, it is not really a culture. It is that person’s instincts operating at scale. Which means it shifts when they leave. When a new VP arrives with different instincts, the decision rules change. Not because anyone updated the design. Because the design was never there. It was a person.

This is why organizations that feel aligned under one leader often lose that alignment when leadership changes. The alignment was not structural. It was personal.

Why Better Communication Does Not Fix This

When alignment breaks down, the default response is more communication. More meetings. More cross-functional time. More joint planning sessions.

These responses reduce tension in the short term. They improve relationships. They give teams a better understanding of each other’s priorities. None of that is wrong.

But better communication does not change the decision rules. Two leaders with a strong relationship still disagree at the handoff when nobody defined who owns the next step. A forecast conversation stays positive on the surface when the culture makes surfacing bad news expensive, regardless of how well the leaders get along. A definition debate gets avoided again because the last attempt cost political capital, even on teams with genuine goodwill between them.

Collaboration manages the friction. It does not change the conditions creating it.

The Cost That Collects in the Calendar

When the decision rules governing critical moments were never deliberately set, leadership absorbs the cost. It shows up in time spent resolving disputes the design should prevent:

• Ownership questions that surface at every handoff because nobody ever formally settled them

• Definition debates that restart each quarter because the answer was never documented and enforced

• Forecast conversations that cover the same ground repeatedly because the culture makes honest disclosure expensive

None of that time appears on any report. It just collects quietly in the calendar of every senior revenue leader managing a culture that nobody deliberately built.

The deeper cost is what that time is not being spent on.

The Question Worth Sitting With

The organizations that sustain alignment through leadership changes, strategy shifts, and pressure do not have unusually talented people or unusually strong relationships. They have decision rules that were set on purpose, applied consistently, and maintained over time so that aligned behavior is the path of least resistance rather than the result of sustained effort.

That kind of culture does not emerge. It is built. And it starts with a question most leadership teams have never formally asked:

What decision rules are currently governing behavior at the moments where our alignment most often breaks down, and did anyone deliberately choose them?

If the answer is unclear, the rules are still there. They are just not the ones anyone would have chosen.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week, Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together

Data fragmentation in a revenue organization is rarely described accurately. The description leaders reach for most often is technical. The systems are not integrated. The data is not clean. The dashboards do not sync. Those descriptions are not wrong. They just name the condition at the wrong level. The systems being out of sync is a symptom. The reason they stay out of sync, quarter after quarter, despite projects and tools and clean-up efforts, is a leadership design condition that technology cannot fix.

When no one governs the standard for how revenue data is defined, owned, and maintained, every tool in the stack reflects that absence faithfully. The dashboard does not lie. It shows exactly what the underlying definitions produce. And when those definitions were set independently, by function, over time, without formal reconciliation, what the dashboard shows is not one version of the business. It is three.

What Fragmented Data Actually Costs

The pipeline review is where the cost becomes visible. But the more expensive version of the problem is not in the meeting. It is in every decision made before it. When sales and marketing are each working from a different definition of what counts as qualified, a different view of which accounts deserve priority, and a different measure of what pipeline health looks like, they do not just report differently. They act differently. Sales pursues segments marketing is not supporting. Marketing funds campaigns against a buyer stage sales has already moved past. Account priorities and campaign priorities diverge because each function is building from a different version of what the business is trying to win.

Each function is doing the right thing from inside its own system. The systems just do not agree. This is what data fragmentation actually costs. Not a bad dashboard. Not a difficult forecast conversation. Compounding behavioral divergence, accruing quietly inside every decision each function makes independently, until a quarter closes short and no one can give a clean account of why.

The Standard Problem Most Organizations Have Not Named

In many B2B revenue organizations, the data fragmentation problem has been diagnosed as a tool problem, a process problem, or a talent problem. Each diagnosis leads to a familiar sequence. Someone gets assigned to fix it. A project gets scoped. The work gets done. The fragmentation returns.

The diagnosis is wrong. The fragmentation is not being produced by a tool gap or a process gap. It is being produced by the absence of a governance decision that most leadership teams have never formally made: who owns the standard for how the business defines, measures, and maintains its revenue data.

Not who builds the dashboards. Not who manages the CRM. Who owns the governing standard itself. Who decides what counts as a qualified lead. Who determines when a deal moves stages. Who enforces consistency when definitions start to drift, as they will when business conditions change and nobody is formally accountable for keeping the standard current.

That accountability for many organizations does not live anywhere on an org chart. It gets absorbed informally by whoever is most capable or most persistent: a sales ops person, a marketing ops analyst, a senior rep who has been around long enough to remember what the definitions used to be. That person is doing work the organization depends on without knowing it depends on them.

The RevOps Reality for Many

RevOps adoption data skews heavily toward technology and SaaS companies. In more established industries, a dedicated RevOps function is the exception, not the norm. That is not a gap that needs to be apologized for. It is the operating condition the governance decision needs to be made inside of. The instinct when data fragmentation becomes disruptive enough is to look for a person who can solve it, often framed as a RevOps hire. That instinct is understandable and not entirely wrong. But organizations that bring in a RevOps function before making the governance decision consistently find that the hire does not deliver what they expected. The function cannot govern what leadership has not yet defined. The hire arrives to a system where nobody has formally designated what counts as true, and spends the first several months doing what capable operators always do in that situation: absorbing the accountability informally and building the standard from scratch without a formal mandate to enforce it.

The governance decision is a leadership decision first. It is the one that says: we are going to name a single governing standard for how this organization measures and manages its revenue data, and we are going to name someone accountable for maintaining it. That decision does not require a title or a function. It requires the leadership team to treat data integrity as a design responsibility rather than an operational nuisance.

Who makes that decision, and what it takes to make it stick, is a longer conversation. But it starts with recognizing that the pipeline review problem, the forecast disagreement problem, and the behavioral divergence problem are all downstream of the same upstream absence.

The Question Worth Sitting With

Data trust in a revenue organization does not begin with better tools. It begins with one shared definition of what matters, applied consistently across every revenue function, and maintained over time.

Most organizations do not have that. Not because they lack the capability to build it. Because no one has made the leadership decision that it needs to exist, and named someone accountable for making it real.

The question worth sitting with before next quarter’s pipeline review is not which dashboard to trust.

It is who in your organization owns the standard the dashboard is built on.

And if the answer is unclear, it has not been formally decided yet. Which means the fragmentation has not been addressed yet either. It has just been managed.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together

When a VP of Sales or VP of Marketing leaves, the organization focuses on the search. Who is the right profile. How fast can the role be filled. What the transition plan looks like.

The question that rarely gets asked is what the incoming leader is about to inherit.

Not the team. Not the targets. The misalignment debt: the accumulated design gaps, the undocumented workarounds, the informal coordination layer that was holding execution together under the leader who just left. That debt does not appear in any handoff document. It does not show up in the role brief. It transfers silently, fully intact, to whoever sits down next.

Leadership transitions are the highest-stakes version of a pattern that runs through every personnel change at every level of a revenue organization. And because the VP-level transition is where the debt is most visible and most expensive, it is the right place to start examining what is actually being passed from one leader to the next.

How Misalignment Debt Transfers

Misalignment debt is not a crisis event. It does not arrive as a sudden failure or a dramatic miss. It accumulates gradually, inside the design of the revenue system itself:

• Incentive structures that reward different outcomes across functions

• Metric definitions that shift depending on who is in the room

• Handoff assumptions that were never formally documented because the two people who agreed on them both left

This is what makes it dangerous. Not its size at any given moment. Its persistence.

Leadership conversations tend to treat misalignment as a people problem. The wrong team. The wrong fit. The wrong culture. That framing is not dishonest — it reflects what the symptoms look like from a leadership position. Friction increases, forecast confidence erodes, execution feels harder than the inputs suggest it should. The obvious variable is the people involved.

The less obvious variable is the system those people are operating inside.

The Shadow Work Layer

When the system has gaps: unclear ownership, competing definitions, undocumented handoff rules. People fill them. Not through policy or process. Through informal coordination, personal knowledge, and the accumulated judgment of operators who have learned to make the system function despite its design. This is shadow work: the invisible layer of effort that keeps execution moving when the formal system cannot.

Shadow work is not inherently a problem. In many organizations it is the difference between acceptable performance and complete breakdown. The problem is what happens to it when personnel change.

Shadow work does not transfer cleanly. It is not in any documentation. It is not in any job description. It lives in the habits, relationships, and institutional memory of the people who built it. When those people leave, take new roles, or are replaced, the shadow work disappears with them. The formal system remains. The informal layer that was holding it together does not.

This is the mechanism behind misalignment debt transfer. Not leadership failure. Not cultural breakdown. The quiet disappearance of the shadow work that was making the system function, leaving behind a formal design that was never sufficient on its own.

How the Debt Compounds

In the mid-market organizations I watch closely, this pattern shows up with a specificity that most leadership conversations miss. The early signals are easy to dismiss:

• A process that used to take two days now takes five

• A handoff that used to be clean now requires a follow-up conversation

• A lead that would have moved smoothly through the funnel now stalls at a stage where nobody owns the next step clearly

• Leaders schedule more syncs to compensate for coordination that used to happen informally

None of those responses address the underlying cause. They add coordination effort to compensate for the missing shadow work. The coordination effort becomes normal. The timeline compression becomes the baseline. The new baseline gets absorbed into what the organization considers acceptable performance.

Each quarter the design goes unexamined, the organization builds more of its operating rhythm around compensating for it. The informal fixes accumulate new layers. New operators learn to work around a system they inherited without fully understanding it. The misalignment debt grows not because the design gets worse, but because the organization adapts to it so thoroughly that the adaptation becomes the system.

The Hidden Talent Cost

There is a less visible cost that compounds alongside the operational drag.

When capable operators spend significant portions of their time on shadow work: reconciling data, translating definitions, manually bridging handoffs. They are not spending that time on the work that requires their actual capability. The best operators in any mid-market revenue organization are typically the ones carrying the heaviest shadow work load, because they are the ones capable enough to do it well.

That is the hidden talent cost of unexamined misalignment debt. It consumes the capacity of the people least likely to complain about it.

The Misdiagnosis That Keeps It Going

When those operators leave, the organization discovers within one to two quarters that performance has degraded in ways that are difficult to explain. The metrics that were holding now slip. The handoffs that were working now stall. Leadership responds by examining:

• The process

• The tools

• The remaining team

They do not typically examine the shadow work that disappeared, because they did not know it existed.

This is the misdiagnosis that keeps the debt compounding. When the symptom of lost shadow work looks like a performance problem and leadership responds with a performance solution, the underlying design remains unchanged. The next capable operator who joins inherits the same gaps. They fill them the same way: informally, invisibly, without documentation. The debt transfers again. The cycle continues.

The Question Worth Sitting With

The question worth asking before the next VP-level search begins is not who is right for the role. It is what that person is about to inherit, and whether the system they are walking into is designed to support execution or designed to consume it.

Most organizations discover the answer to that question only after the new leader has spent a quarter compensating for a design they did not create, under pressure from results they did not set, inside a system that transferred its debt to them without acknowledgment.

The debt does not announce itself. It does not wait to be acknowledged.

It compounds, quietly, until the organization decides to examine the design.

That decision gets more expensive the longer it waits.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together